2-Chlorobenzylamine → HCID 22612355, compound

Participants

Reaction Steps

To a stirred solution of 2-(3-Carbamoyl-phenoxy)-N-(2-chloro-benzyl)-nicotinic acid (0.300 grams, 1.25 mmole), o-chlorobenzylamine (0.195 grams, 1.375 mmole), and 1-hydroxybenzotriazole hydrate (0.203 grams, 1.50 mmole) in dry dimethylformamide (3 ml) was added 1-(3-dimethylamino)-propyl)-3-ethylcarbodiimide hydrochloride (0.311 grams, 1.63 mmole) and stirred over night. The mixture poured into 100 ml water and extracted with ethyl acetate. The combined extracts were washed with 1 N NaOH, water and brine, dried over Na2SO4, filtered and concentrated to give a white solid that was purified by chromatography on silica gel eluting with 7% methanollmethylene chloride. Recrystalization from ethyl acetate/hexane gave a white solid (0.239 g). M.P. 153-155° C.; Anal. calcd. for C20H16N3O3Cl: C, 62.91; H, 4.22; N, 11.01. Found: C, 62.92; H, 4.30; N, 11.09.

Provenance & Evidence